Hydrochloric Acid → 3-(Dimethylamino)-1-(2-thienyl)-1-propanone

HRID 1024483Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1024483
[CH3:1][N:2]([CH3:12])[CH2:3][CH2:4][CH:5]([OH:11])[C:6]1[S:7][CH:8]=[CH:9][CH:10]=1.C(C1SC=CC=1)(=O)C.Cl.CNC.C=O.Cl>C(O)(C)C>[S:7]1[CH:8]=[CH:9][CH:10]=[C:6]1[C:5]([CH2:4][CH2:3][N:2]([CH3:1])[CH3:12])=[O:11]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 69202-AcetylthiopheneHCID 10473Dimethylamine, hydrochlorideHCID 115864093-(Dimethylamino)-1-(2-thienyl)-1-propanol

Produkt 1

HCID 4082573-(Dimethylamino)-1-(2-thienyl)-1-propanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

One example of a known method for producing N,N-dimethyl-3-hydroxy-3-(2-thienyl)propanamine uses the reaction between 2-acetylthiophene and dimethylamine hydrochloride in isopropanol in the presence of paraformaldehyde and hydrochloric acid to obtain (2-thienyl)(2-dimethylaminoethyl)ketone, and the (2-thienyl)(2-dimethylaminoethyl)ketone is reduced using sodium borohydride in ethanol (JP 7-188065 A). If N-monoalkyl-3-hydroxy-3-(2-thienyl)propanamine is produced in the same method as described above except that a monoalkylamine hydrochloride is used instead of the dimethylamine hydrochloride, since the production intermediate, i.e., (2-thienyl)(2-monoalkylaminoethyl)ketone, is unstable, an N,N′,N″-alkyl-bis[1-[3-oxo-3-(2-thienyl)propane]]amine, which is a dimer, is produced, and therefore the yield of the N-monoalkyl-3-hydroxy-3-(2-thienyl)propanamine obtained after the reduction using sodium borohydride is low.

Quellen und Nachweise

ORD-Eintrag
ord-a588b76f7e0144fcb43006ca7956443c
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722906B2

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